In late March 2010, President Obama’s national security adviser, James L. Jones, summoned Richard C. Holbrooke to the White House for a late-afternoon conversation. The two men rarely had one-on-one meetings, even though Holbrooke, the State Department’s point man for Afghanistan, was a key member of Obama’s war cabinet.

As Holbrooke entered Jones’s West Wing office, he sensed that the discussion was not going to be about policy, but about him. Holbrooke believed his principal mission was to accomplish what he thought Obama wanted: a peace deal with the Taliban. The challenge energized Holbrooke, who had more experience with ending wars than anyone in the administration. In 1968, he served on the U.S. delegation to the Paris peace talks with North Vietnam. And in 1995, he forged a deal in the former Yugoslavia to end three years of bloody sectarian fighting.

The discussion quickly wound to Jones’s main point: He told Holbrooke that he should start considering his “exit strategy” from the administration.

As he left the meeting, Holbrooke pulled out his trump card — a call to Secretary of State Hillary Rodham Clinton, who was traveling in Saudi Arabia. The following week, Clinton went to see Obama armed with a list of Holbrooke’s accomplishments. “Mr. President,” she said, “you can fire Richard Holbrooke — over the objection of your secretary of state.” But Jim Jones, Clinton said, could not.

Obama backed down, but Jones didn’t, nor did others at the White House. Instead of capitalizing on Holbrooke’s experience and supporting his push for reconciliation with the Taliban, White House officials dwelled on his shortcomings — his disorganization, his manic intensity, his thirst for the spotlight, his dislike of Afghan President Hamid Karzai, his tendency to badger fellow senior officials. At every turn, they sought to marginalize him and diminish his influence.

The infighting exacted a staggering cost: The Obama White House failed to aggressively explore negotiations to end the war when it had the most boots on the battlefield.

Even after Obama decided not to fire Holbrooke, Jones and his top deputy for Afghanistan, Lt. Gen. Douglas E. Lute, kept adding items to a dossier of Holbrooke’s supposed misdeeds that Lute was compiling. They even drafted a cover letter that called him ineffective because he had ruined his relationships with Karzai, the U.S. ambassador in Kabul and officials in the Pakistani government. Lute told NSC staffers that he and Jones planned to use the information to persuade the president to override Clinton’s objection.

In the interim, Jones and Lute sought to put Holbrooke into a box. Officials at the National Security Council would schedule key meetings when Holbrooke was out of town. When they didn’t want him to travel to the region, they refused to allow him to use a military airplane. They even sought to limit the number of aides Holbrooke could take on his trips.

Lute and other NSC staffers cooked up their most audacious plan to undercut Holbrooke shortly before Karzai’s visit to Washington in April 2010. They arranged for him to be excluded from Obama’s Oval Office meeting with the Afghan leader, and then they planned to give Obama talking points for the session that would slight Holbrooke. Among the lines they wanted the president to deliver to Karzai: Everyone in this room represents me and has my trust. The implication would be that Holbrooke, who would not be present, was not Obama’s man. The scheme was foiled when Clinton insisted that Holbrooke attend the session.

With Clinton protecting him, Holbrooke spent far less time worrying about how to save his job than Lute spent trying to fire him. “Doug is out of his depth fighting with me,” Holbrooke told one of his aides. “The White House can’t afford to get rid of me.”

Obama could have ordered a stop to the infighting; after all, he favored a negotiated end to the war. But his sympathies lay with his NSC staffers — Holbrooke’s frenetic behavior was the antithesis of Obama’s “no-drama” rule. The president never granted Holbrooke a one-on-one session in the Oval Office, and when he traveled to Afghanistan in March 2010, he took more than a dozen staffers, but not Holbrooke, who was not even informed of the trip in advance. During the Situation Room sessions to discuss Gen. Stanley A. McChrystal’s request for more forces in late 2009, Obama kept his views about surging to himself, but he was far less reticent about Holbrooke. At the start of one meeting, Holbrooke gravely compared the “momentous decision” Obama faced to what Lyndon B. Johnson had grappled with during the Vietnam War. “Richard,” Obama said, “do people really talk like that?”

The president’s lack of support devastated Holbrooke’s loyal staff members, who were just as skeptical of the military’s counterinsurgency strategy as Lute and others in the White House were. “The tragedy of it all is that Richard’s views about all of this stuff — about the surge, about Pakistan and about reconciliation — were probably closer to the president’s than anyone else in the administration,” said former Holbrooke senior adviser Vali Nasr, now the dean of the Johns Hopkins School of Advanced International Studies. “If the president had wanted to, he could have found a kindred spirit in Richard.”

No clear path to peace

To Holbrooke, a towering man with an irrepressible personality, brokering a deal with the Taliban was the only viable strategy to end the war.

He was convinced that the military’s goal of defeating the Taliban would be too costly and time-consuming, and the chances of success were almost nil, given the safe havens in Pakistan, the corruption of Karzai’s government and the sorry state of the Afghan army.

Obama told his aides that he was interested in a peace deal, and less than two months after he took office, the president said publicly that he was open to seeking reconciliation with the Taliban, comparing such an effort to a U.S. initiative to work with former Sunni militants in Iraq who were willing to break with al-Qaeda.

His comments alarmed top military and intelligence officials. Adm. Mike Mullen, the chairman of the Joint Chiefs of Staff, and Gen. David H. Petraeus, chief of U.S. Central Command, thought it was too soon even to talk about talking. They wanted to commit more troops first and then talk, but only to Taliban leaders who agreed to surrender. CIA officials argued that the United States could not negotiate with the Taliban until its leadership denounced al-Qaeda.

There was no clear path for Holbrooke to achieve peace talks. The Taliban had no office, mailing address, or formal structure. It was not clear that its leader, the reclusive Mullah Mohammed Omar, wanted to talk — in 2009, the Taliban appeared to be winning — or whether he and his fellow mullahs would accept the United States’ conditions for negotiations: that they renounce violence, break with al-Qaeda and embrace the Afghan constitution.

Even if they did, would the terms be acceptable to the Karzai government? What about Pakistan and other neighboring powers? If Holbrooke was going to have any chance of success, he needed the backing of others in the administration, starting with the president.

But the White House never issued a clear policy on reconciliation during the administration’s first two years. Instead of finding common purpose with Holbrooke, White House officials were consumed with fighting him. Jones and Lute hated the thought of Holbrooke basking in the spotlight as he did after peace in the Balkans. They wanted him out of the way, and then they would chart a path to peace.

Staffs at war

At the White House, most of the day-to-day combat with Holbrooke was led by Lute. He had joined the George W. Bush White House as an active-duty three-star general to serve as the Iraq and Afghanistan war czar. When Obama became president, he had decided to keep Lute around, in part because he could warn them if his fellow generals were trying to pull a fast one on the new crop of civilians.

Lute spent much of his time organizing meetings and compiling data that showed how the war was being lost. He believed his work was vital, and he thought that Holbrooke needed to follow his lead. But Holbrooke believed Lute needed to take orders from him, not the other way around. Holbrooke began to treat Lute as an errand boy, sometimes calling four times in an hour.

Lute’s resentment grew with each request that Holbrooke’s office ignored and each State Department memo that had to be revised by the NSC staff. Before long, the two men’s staffs were in open warfare.

Senior officials at the White House let the fighting persist. Holbrooke had no friends on Team Obama. Denis McDonough, then the NSC chief of staff, had been angered by Holbrooke’s strong-arming of Democratic foreign policy experts to support Clinton during the 2008 Democratic presidential primaries. Ben Rhodes, the NSC’s communications director, claimed to colleagues that Holbrooke was the source of leaks of sensitive matters to journalists. And Vice President Biden’s dislike of him dated to Bill Clinton’s administration.

With his frequent references to Vietnam and flair for the dramatic, Holbrooke’s style left him the odd man out with White House advisers. If Obama or Clinton was not at a meeting, Holbrooke insisted on dominating the conversation. He was a throwback to a time when men like Henry Kissinger and George Kennan held unrivaled sway over policy.

“He spoke like a man who just left talking to Kennan — and walked into 2009, still in black and white, with his hat on,” said Vikram Singh, one of his top deputies. “Sometimes it was a bunch of bulls---, and sometimes it was a bunch of wisdom. But if you were this young crowd that came in with Barack Obama, it seemed cartoonish. . . . They weren’t able to hear what he was saying because they were distracted by the mannerisms and the way he did things — and he couldn’t figure that out.”

The only one who understood him was Clinton. She was indebted to Holbrooke for his support during the 2008 primaries and for delivering peace in the Balkans, the most significant diplomatic breakthrough of Bill Clinton’s presidency. She tolerated his idiosyncrasies because she was confident that he’d deliver a breakthrough in Afghanistan.

‘Anybody but Richard’

As the White House and Holbrooke bickered, promising leads withered.

In July 2009, King Abdullah of Saudi Arabia sent a personal message to Obama asking him to dispatch someone to meet with a group of Taliban emissaries who had opened up a rare line of communication with the Saudi intelligence service. The Saudi intelligence chief had already met with the U.S. ambassador to Riyadh and the CIA station chief there to discuss the initiative, but the Saudis deemed the discussions so promising that Abdullah asked his ambassador to Washington to discuss the matter with Jones. Holbrooke figured the overture was worth pursuing. But the offer languished at the NSC.

The NSC eventually expressed support for reconciliation in the spring of 2010, but with a twist: Lute favored a U.N. envoy to lead the effort. His preferred candidate was former Algerian foreign minister Lakhdar Brahimi, who had served as a U.N. special representative to Afghanistan. Lute’s plan relegated Holbrooke to a support role.

Lute argued that Brahimi had Karzai’s trust and that he could deal with Iran and Pakistan in ways that a U.S. diplomat couldn’t. There was also the opportunity to shift blame for failure. “If this doesn’t work,” he told colleagues, “do we want to own it or do we want the U.N. to?”

It seemed a masterstroke — except that the Afghan and Pakistani governments despised the idea. Everyone in the region wanted the United States to lead the effort. They knew the United Nations was powerless.

Clinton was furious with Lute. “We don’t outsource our foreign policy,” she declared to Holbrooke and his staff. Then she went to Obama to kill the idea.

Even with Brahimi rejected, Lute resumed his efforts to find someone else to take charge of reconciliation, this time focusing on retired American diplomats.

“It was driven by hatred,” said an NSC staffer who worked for Lute. “Doug wanted anybody but Richard.”

Shift on reconciliation

As Washington officials quarreled, a quiet shift was occurring at the NATO headquarters in Kabul. While other military leaders opposed reconciliation, McChrystal began softening to the idea. His thinking was shaped by Christopher Kolenda, an astute Army colonel who had been working on a program to provide resettlement and job-training to low-level insurgents who wanted to stop fighting. In December 2009, Kolenda explained to McChrystal how Mullah Omar’s annual messages at the Eid-al-Fitr holiday had become more sophisticated and moderate. The Taliban, he told the general, “is opening the aperture for a different outcome.”

As spring turned to summer, McChrystal became a believer. He realized that the United States would not be able to get an outright military victory, and the Afghan government would not be able to get an outright political victory, so a peace deal was the only solution. McChrystal didn’t want to let up on the Taliban just yet, but he said he was ready to “clearly show them there’s daylight if you go to it.” In early June, he directed Kolenda to prepare a briefing for Karzai on reconciliation.

Later that month McChrystal was fired over comments he and some top aides made disparaging American civilian officials. Obama tapped Petraeus, who led the effort to beat back insurgents in Iraq, to replace McChrystal and energize the war effort. When Petraeus arrived in Kabul, he ordered a halt to the military’s reconciliation activities. He told his subordinates that if the Americans applied enough military pressure, the insurgents would switch sides in droves. To some in the headquarters, it sounded as if he wanted to duplicate what had occurred in Iraq’s Anbar province, when Sunni tribesmen had eventually decided to forsake al-Qaeda and side with the United States. Although Obama had mentioned the Sunni Awakening as a possible model in his first public comments on reconciliation, his views had evolved by the summer of 2010. He told his war cabinet that he was open to pursuing negotiations with the enemy, the likes of which never occurred in Iraq. Petraeus’s approach was more akin to accepting a surrender from a rival under siege.

At the White House, Lute and other NSC staffers were so obsessed with Holbrooke that they failed to marshal support among the war cabinet to force Petraeus to shift course. On a visit to Kabul in October 2010, Holbrooke sought to lobby Petraeus directly.

“Dave, we need to talk about reconciliation,” Holbrooke said to Petraeus as they got into an armored sport-utility vehicle, according to Holbrooke’s recollection to his staff.

Holbrooke died of a torn aorta on Dec.13, 2010. His memorial service in Washington was held on a chilly January afternoon in the packed opera house of the John F. Kennedy Center for the Performing Arts. Obama delivered a eulogy. So did Bill and Hillary Clinton and former U.N. Secretary General Kofi Annan.

The differences in their speeches revealed how distant Holbrooke’s relationship with Obama had been. The sitting president spoke with eloquence, but his remarks sounded stiff, devoid of a single personal anecdote.

Hillary Clinton, by contrast, celebrated the very traits that Jones, Lute and others had derided: “There are many of us in this audience who’ve had the experience of Richard calling 10 times a day if he had to say something urgent, and of course, he believed everything he had to say was urgent. And if he couldn’t reach you, he would call your staff. He’d wait outside your office. He’d walk into meetings to which he was not invited, act like he was meant to be there, and just start talking.”

But it wasn’t until the following month, at a memorial event for Holbrooke in New York, that Clinton said what he really would have wanted to hear: “The security and governance gains produced by the military and civilian surges have created an opportunity to get serious about a responsible reconciliation process.” The United States finally had indicated a clear desire to negotiate with the Taliban.

Clinton also revealed a crucial shift in U.S. policy. The three core American requirements — that the Taliban renounce violence, abandon al-Qaeda and abide by Afghanistan’s constitution — were no longer preconditions for talks but “necessary outcomes of any negotiation.” That meant the Taliban could come as they were. It was the speech that Holbrooke had sought to deliver for a year. Ironically, the only man in the administration to negotiate an end to a war had been an impediment to ending this war.

With Holbrooke gone, Lute stopped insisting on an envoy from outside the State Department. The White House empowered Holbrooke’s successor, diplomat Marc Grossman, to pursue negotiations. And Pentagon and CIA officials ceased their opposition to the prospect of talks with the Taliban.

Although military gains across southern Afghanistan had put the United States in a slightly better negotiating position by that February, nothing had changed fundamentally since Holbrooke’s last push to persuade others in the Obama administration to embrace a peace plan. Nothing except his death.

For more information about “Little America” and to read another excerpt, go to rajivc.com.

Rajiv Chandrasekaran is a senior correspondent and associate editor. He has served as national editor and as bureau chief in Baghdad, Cairo and Southeast Asia.

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